Category: ethers-buliding-blocks

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1535-73-5, name is 3-Trifluoromethoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Trifluoromethoxyaniline

Example 6 : (+/-) 3-{f(3-trifluoromethoxyphenyl)amino1carbonyl)-1 ,2,2- trimethylcvclopentanecarboxylic acidA mixture of (+/-) camphoric acid anhydride (0.92 g, 5.05 mmol), anhydrous sodium acetate (0.5Og, 6.09 mmol) and 3-(trifluoromethoxy)aniline (1.015 g, 5.73 mmol) were heated in an oil bath at 140cC for 2 hours. The mixture was removed from the oil bath to cool sufficiently to add water (4 ml) and ethyl acetate (4ml). The mixture was stirred with heating to dissolve the solids before diluting with more ethyl acetate (20ml) and dilute hydrochloric acid (20 ml, 1M). The organic layer was taken and partially evaporated under vacuum to give a viscous oil. The oil was dissolved in ethyl acetate (6 ml) and then petroleum ether (6 ml, 40-60) added. The crystals that formed were collected and washed with more ethyl acetate/petroleum ether (1 :3, 6 ml) and dried under vacuum to give (+/-) 3-{[3-trifluoromethoxyphenyl)amino]carbonyl}- 1 ,2,2-trimethylcyclopentanecarboxylic acid as a white powder (0.97 g, 53percent yield) ; 1 H-NMR (400 MHz1 d6-DMSO) : 612.22 p.p.m. (s, 1 H), 10.01 (s, 1 H), 7.84 (S1 1 H)1 7.56 (m, 1 H)1 7.46 (t, J = 8 Hz, 1 H), 7.04 (m, 1 H), 2.91 (t, J = 9.4 Hz, 1 H), 2.49 (m, 1 H), 2.08 (m, 1 H)1 1.79 (m, 1 H), 1.46 (m, 1 H), 1.22 (s, 6H), 0.82 (S, 3H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1535-73-5.

Reference:
Patent; MERLION PHARMACEUTICALS SA; MERLION PHARMACEUTICALS PTE LTD; WO2008/17840; (2008); A1;,
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Application of 7664-66-6,Some common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of 3′,4′-dichloro-4-fluorobiphenyl-3-carbonitrile (173 mg, 0.650 mmol), 4-isopropoxyaniline (108 mg, 0.715 mmol), and KOtBu (154 mg, 1.375 mmol) in DMSO (4mL) was stirred at rt for 1.5h, The mixture was diluted with ethyl acetate, washed with H2O and brine, and then dried over Na2SO4. The solvent was removed and the product was purified by silica gel chromatography (eluting with hexane containing 0 to 8% ethyl acetate) followed by preparative HPLC (100 x 30 mm Luna C18 column, flow rate 42 ml permin, gradient elution starting with A:B =50:50 and ending with A:B =0: 100 [A = 10 mM NH4OAc in 5% aqueous acetonitrile; B = IO mM NH4OAc in 95% aqueous acetonitrile] over 20 min). This afforded 99 mg of 3′,4′-dichloro-4-(4-isopropoxyphenylamino)-biphenyl-3- carbonitrile which still contained some impurities according to the LC/MS but was used as such for next step. MS (ESI) m/z 397.1 (M+H).

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PURANDARE, Ashok, Vinayak; BATT, Douglas, G.; LIU, Qingjie; JOHNSON, Walter, L.; MASTALERZ, Harold; ZHANG, Guifen; ZIMMERMANN, Kurt; WO2010/80474; (2010); A1;,
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Electric Literature of 10385-36-1, A common heterocyclic compound, 10385-36-1, name is 1-Bromo-2,3,4-trimethoxybenzene, molecular formula is C9H11BrO3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

The title compound was prepared according to the procedure described for 10, starting from compound 19a. Colorless oil (crude). This was used in the next step without further purification

The synthetic route of 10385-36-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nakamura, Masaharu; Kajita, Daisuke; Matsumoto, Yotaro; Hashimoto, Yuichi; Bioorganic and Medicinal Chemistry; vol. 21; 23; (2013); p. 7381 – 7391;,
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588-96-5, name is p-Bromophenetole, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of p-Bromophenetole

General procedure: The Teflon-lined sealed tube (20 mL) was charged with a 1,4-dioxane solution of sodium fluoroalkoxide RFONa [freshly prepared from fluoroalkanol RFOH (3.3(n + 1) mmol) and Na (3.0 (n + 1) mmol) in 1,4-dioxane (5 mL)], unactivated arylbromide ArBrn (3.0 mmol), CuBr (0.3n mmol) and DMF (3.0n mmol). The sealed tube was heated to 110 C and stirred for 6 h. After the completion of reaction, the concentration of the mixture in vacuo gave a residue, to which was added methyl tert-butyl ether (MTBE, 20 mL) and diluted hydrochloric acid (10 mL, 1.0 mol/L). The organic phase was separated, and the aqueous phase was extracted with MTBE (10 mL 9 3). The combined organic layer was dried over anhydrous MgSO4, andthen concentrated in vacuo to supply a crude product. Lastly, the purification of the crude product provided the desired product via column chromatography on silica gel (eluents: petroleum ether/ethyl acetate 20:1).

The synthetic route of 588-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Ying; Li, Yu-Dao; Chen, Cheng; Zhao, Jian-Hong; Liu, Hong-Wei; Liao, Dao-Hua; Ji, Ya-Fei; Research on Chemical Intermediates; vol. 42; 3; (2016); p. 2525 – 2537;,
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Some common heterocyclic compound, 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, molecular formula is C7H5BrF3NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. HPLC of Formula: C7H5BrF3NO

b) 5-Bromo-2-trifluoromethoxyphenol A solution of 210 mmol of sodium nitrite in 120 ml of water is added dropwise to a suspension of 200 mmol of 5-bromo-2-trifluoromethoxyaniline in 500 ml of ethanol and 50 ml of conc. HCl at 0C. The reaction mixture is stirred at 5C for 1.5 hours. The reaction mixture is slowly added dropwise to a solution of 135 ml of conc. sulphuric acid in 2.8 l of water and stirred under reflux overnight. The reaction mixture is extracted with diethyl ether (3x) – the combined organic phases are washed with water and 1 M sodium bicarbonate solution and then extracted with 2N NaOH (2x). The combined aqueous phases are acidified with conc. HCl and extracted with diethyl ether (3x). The combined organic phases are washed with water, dried with sodium sulphate and evaporated. The crude title compound is obtained from the residue.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 886762-08-9, its application will become more common.

Reference:
Patent; Speedel Experimenta AG; EP1958666; (2008); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1535-75-7, name is 2-(Trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2-(Trifluoromethoxy)aniline

General procedure: Acetamides (1a-1x, 1ab, 1ac and 1ba-1bc). To a solution of 2-phenylacetic acid (7.0mmol), 2-(trifluoromethoxy)aniline (7.7mmol) in anhydrous CH2Cl2 (25mL) were added EDCI (1.745g, 9.1mmol) and DMAP (256.6mg, 2.1mmol). The reaction mixture was stirred at room temperature overnight, diluted with HCl (1M) aqueous solution, and extracted with CH2Cl2 (3×25mL). The combined organic phase was washed with saturated NaHCO3 aqueous solution and brine, dried over anhydrous Na2SO4, and concentrated under vacuum. Purification by flash chromatography (Silica gel, petroleum ether: ethyl acetate=50: 1 as eluent) gave the corresponding 2-phenyl-N-[2-(trifluoromethoxy)phenyl]acetamide compound.

The synthetic route of 1535-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Xiao-Jing; Zhao, Jie; Sun, Xin; Liu, Ji-Kai; Wu, Bin; Tetrahedron; vol. 73; 25; (2017); p. 3463 – 3477;,
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Application of 19500-02-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 19500-02-8 as follows.

Step 3: synthesis of (2-amino-4-methoxy-3-methylphenyl)(methyl)ketone (4). A solution Of BCl3 (1.0 M, 200 mL, 200 mmol) in CH2Cl2 was slowly added under nitrogen to a solution of 3-methoxy-2-methylaniline (26.0 g, 190 mmol) in xylene (400 mL). The temperature was monitored during the addition and was kept below 100C. The reaction mixture was stirred at 5°C for 0.5 h. Then, dry acetonitrile (13 mL, 246 mmol) was added at 5°C. After 0.5 h at 5°C, the solution was transferred into a dropping funnel and slowly added at 5°C to a suspension OfAlCl3 (26.7 g, 200 mmol) in CH2Cl2 (150 mL). After 45 min at 5°C, the reaction mixture was heated at 700C under a nitrogen stream. After evaporation Of CH2Cl2, the temperature of the reaction mixture reached 65°C. After 12 h at 65°C, the reaction mixture was cooled at 00C, poured onto ice (300 g), and slowly heated to reflux for 7h. After 2 days at room temperature, 6 N NaOH (50 mL) was added. The pH of the resulting solution was 2-3. The xylene layer was decanted. The organic layer was extracted with CH2Cl2. The xylene and CH2Cl2 layers were combined, successively washed with water, IN NaOH, and brine, dried (Na2SO4) and evaporated. The residue was triturated in diisopropyl ether at O0C, filtered off and washed with diisopropylether to give 13.6 g (40 percent) of the title product as a yellowish solid: m/z = 180 (M+H)+.

According to the analysis of related databases, 19500-02-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; MEDIVIR AB; WO2008/96002; (2008); A1;,
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Related Products of 202865-80-3, A common heterocyclic compound, 202865-80-3, name is 4-Bromo-2-fluoro-1-isopropoxybenzene, molecular formula is C9H10BrFO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a mixture of 2-amino-5-ethyl-3-(4-methylphenoxy)pyrazine (55.0 mg, 0.240 mmol) and dioxane (1 mL) were added 4-bromo-2-fluoro-1-isopropoxybenzene (61 mg, 0.26 mmol), tris(dibenzylideneacetone)(0) (2.8 mg, 0.0030 mmol), 4,5-bis(diphenylphosphine)-9,9-dimethylxanthene (4.2 mg, 0.0072 mmol) and sodium phenoxide trihydrate (61 mg, 0.36 mmol), and the resulting mixture was heated at reflux for 4 hours. To the reaction mixture was added saturated aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate. The extract was washed by brine, dried over anhydrous sodium sulphate, and concentrated in vacuo. The resulting residue was purified by reversed-phase HPLC (0.3% formic acid/acetonitrile) to give 5-ethyl-2-(3-fluoro-4-isopropoxyphenylamino)-3-(4-methylphenoxy)pyrazine (17 mg, Yield: 18%) as pale brown solid. 1H-NMR (delta ppm TMS/DMSO-d6): 1.05 (3H, t, J=7.5 Hz), 1.26 (6H, d, J=5.8 Hz), 2.33 (3H, s), 2.44 (2H, q, J=7.5 Hz), 4.45-4.52 (1H, m), 705-7.17 (3H, m), 725 (2H, d, J=8.6 Hz), 7.55-7.61 (1H, m), 7.69 (1H, s), 7.85-7.91 (1H, m), 8.93 (1H, s).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; SHIONOGI & CO., LTD.; Kai, Hiroyuki; Endoh, Takeshi; Jikihara, Sae; Horiguchi, Tohru; US9212130; (2015); B2;,
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Electric Literature of 1535-73-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1535-73-5 as follows.

General procedure: An equimolar mixture of trifluoromethoxyaniline 1 or 2 (5.65 mmol) and the corresponding activated enol ether 3a-h was heated under reflux for 2-120 min (TLC detection). If necessary, methanol or ethanol was used as solvent. Once the reaction was complete, it was cooled to room temperature and the solids formed were separated by suction, washed with hexanes and dried to give enamines 4-5a-h. Isolated enamines 4-5a-h were characterized and used in the subsequent steps.

According to the analysis of related databases, 1535-73-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Plevova, Kristina; Briestenska, Katarina; Colobert, Francoise; Mistrikova, Jela; Milata, Viktor; Leroux, Frederic R.; Tetrahedron Letters; vol. 56; 36; (2015); p. 5112 – 5115;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1758-46-9, name is 2-Phenoxyethylamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Phenoxyethylamine

General procedure: A solution of 2-phenoxyethylamine (1.31 mL, 10 mmol) in methanol (10 mL) was added to a solution of triethylamine(Et3N) (2.76 mL, 20 mmol) in methanol (10 mL) at 0 C. A solution of 2-chloropyridine (3.80 mL, 40 mmol) in methanol(10 mL) was then added at 0 C under N2. After being stirred for 30 min, the reaction mixture was heated to 25 C and stirred for 3 days. Then, the solvent was evaporated under reduced pressure to afford a yellow solid L1 washed with methanol and dried under vacuum.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1758-46-9.

Reference:
Article; Wang, Jun; Liu, Jinyi; Chen, Liduo; Lan, Tianyu; Wang, Libo; Transition Metal Chemistry; vol. 44; 7; (2019); p. 681 – 688;,
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